Top Five Things That I Learned as a Serial Entrepreneur

By Amy Guarino ‘83

“...Two roads diverged in a wood, and I —
I took the one less traveled by, 
And that has made all the difference…” 
                The Road Not Taken by Robert Frost

After graduating from Notre Dame, I accepted a sales role at IBM. As a second-generation IBM’er, I assumed that I would have a 30+ year career with Big Blue. I loved working at IBM, but living in California opened my eyes to all of the wonderful opportunities in Silicon Valley that would allow me to live life to the fullest. With all of these options, I put aside my assumptions and decided to take the leap into entrepreneurship.

I am now at my eighth small company. I have been blessed with multiple exits including two IPOs, two unicorns, lots of acquisitions, and one spectacular failure. Through all of those experiences, I have learned so many lessons that have helped in navigating my career path. Here are the top five things I’ve learned as a resident of the start-up world:   

No. 1 — Take risks. Be brave.
I still remember the words of Fr. John Dunne, my senior-year theology professor: “If I must die someday, what can I do to satisfy my desire to live?” He reminded us that we should live each day to the fullest and take some risks. A little bravery can take you far, in business and in life. 

No. 2 — Successful people rise in pairs. 
When you commit to a career in start-ups, you own your career. Life is easier if you can find a great person or two who shares a similar outlook or vision, so find a superstar and hang on. If that person also complements your skills and experiences, even better. Connect with fellow alumni in the Alumni Business Directory on IrishCompass.

No. 3 — Go for the right company, not the title. 
After working at a couple of start-ups, you get smarter about knowing which companies will succeed. As an investor, you should evaluate a potential company. Ask yourself these five questions: 1. Is there a big (really big) market opportunity for this solution? 2. Do they have the right investors to support their plans? 3. Do they have the right management team? 4. Is the product or solution a “have to have” vs. a “nice to have”? 5. Do they have buzz? If you can tick most of those boxes, then you have the makings of a great opportunity. If you can join the company in a role where you are able to leverage your strengths, the company should recognize that contribution and you will grow with the company. 

No. 4 — It’s all about the network. 
The key to networking is to help someone else first. If you invest in that network, it will become an incredible flywheel and will support you, your companies, and your colleagues. You can tap into the powerful Notre Dame network on IrishCompass.

No. 5 — Get comfortable with being uncomfortable. 
If you are uncomfortable, it’s a good thing. You are growing. Think big. Start small. Start now.


Amy Guarino ’83 is a global, strategic, COO, go-to-market executive, board member and advisor, who creates and builds tech companies, markets, and partnerships to drive billion-dollar growth through strong business acumen, operations, IPOs, acquisitions, sales, and marketing.

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